Benzopyranones, processes for their preparation and their use

Abstract

Described are 2H-1-benzopyran-2-ones (coumarin derivates) of general formula (I), ##STR1## wherein R 1 is a hydroxyl group, a lower-alkoxy group, a cycloalkoxy group with 4 to 6 C-atoms or the alkyl- or arylsulphonyloxy group R 6 --SO 2 O--; R 2 and R 3 , independently of each other, are hydrogen atoms, hydroxyl groups, lower-alkoxy groups or cycloalkoxy groups with 4 to 6 C-atoms; R 4 is a hydrogen atom, a lower-alkyl group with 1 to 4 C-atoms or a phenyl group; Y is a nitrogen atom, a CH group or a COH group; R 5 is a phenyl, naphtyl, pyridinyl or pyrimidinyl group which may optionally be substituted by one or two C 1 -C 5 alkyl groups, by one or two halogen atoms, by a halogen and C 1 -C 5 alkyl together, by perfluoroalkyl with 1 to 3 C-atoms, by C 1 -C 5 alkoxy, by hydroxy, by methylenedioxy or by nitro; R 6 is a lower-alkyl group, a cycloalkyl group with 4 to 6 C-atoms or a phenyl group which may optionally be substituted by one or two C 1 -C 5 alkyl groups, by one or two halogen atoms, or by perfluoroalkyl with 1 to 3 C-atoms; and n=1 to 4; plus their addition compounds with physiologically tolerated acids. Also described are methods of preparing these compounds, novel intermediates in their preparation and methods of preparing such intermediates. The novel coumarin derivatives described possess a neuroprotective and psychopharmacological action. The invention also concerns pharmaceuticals containing these compounds.

We claim: 
     
       1. A 2H-1-benzopyran-2-one having of the formula I, ##STR9## wherein: R 1  is a hydroxy radical, an alkoxy radical with 1 to 5 C atoms, a cycloalkoxy radical with 4 to 6 C atoms, or an alkyl-or arylsulphonyloxy radical R 6  --SO 2  O--, R 2  and R 3  are, independently of one another, a hydrogen atom, hydroxy radical, alkoxy radical with 1 to 4 C atoms, or a cycloalkoxy radical with 4 to 6 C atoms,   R 4  is a hydrogen atom, an alkyl group with 1 to 4 C atoms, or a phenyl radical,   Y is a nitrogen atom, a CH group or a COH group,   R 5  is a phenyl, naphthyl, pyridinyl or pyrimidinyl radical, which is optionally substituted with in each case one or two C 1  -C 5  alkyl groups, with in each case one or two halogen atoms, with halogen and simultaneously C 1  -C 5  alkyl, with perfluoroalkyl with 1 to 3 C atoms, C 1  -C 5  alkoxy, hydroxy, methylenedioxy or nitro,   R 6  is an alkyl radical with 1 to 5 C atoms, a cycloalkyl radical with 4 to 6 C atoms or a phenyl radical, which is optionally substituted with in each case one or two C 1  -C 5  alkyl groups, with in each case one or two halogen atoms or with perfluoroalkyl with 1 to 3 C atoms, and   n is an integer from 1 to 4; or pharmaceutically compatible acid addition salts thereof, with the exception however of 7,8-dimethoxy-4-methyl-3-[(4-phenyl-1-piperazinyl)methyl]-2H-1-benzopyran-2-one.     
     
     
       2. A compound according to claim 1, wherein in said formula I R 1  is a hydroxy, methoxy, ethoxy, propyloxy or ethane sulphonyloxy radical,   R 2  and R 3  are, independently of one another, a hydrogen atom, a hydroxy or alkoxy radical with 1 to 3 C atoms,   R 4  is a methyl group,   Y is a nitrogen atom, a CH group or a COH group,   R 5  is a phenyl radical optionally substituted with hydroxy, methoxy, ethoxy, methyl, fluoro or trifluoromethyl, and   n=2 and the addition compounds thereof with physiologically compatible acids.     
     
     
       3. A pharmaceutical preparation comprising a pharmaceutically effective amount of at least one compound as claimed in claim 1 or claim 2, together with a pharmaceutically acceptable carrier.